Molecular structure of Piloty′s Acid, CAS Number: 599-71-3
Piloty′s Acid (CAS 599-71-3)
Alternate Names:
Benzenesulphonydroxamic Acid
Application:
Piloty′s Acid is a highly used donor of HNO
CAS Number:
599-71-3
Purity:
≥98%
Molecular Weight:
173.19
Molecular Formula:
C6H7NO3S
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Piloty′s Acid is one of the most used nitroxyl (HNO) donors, decomposing to form HNO and benzenesulfinate anion under basic conditions. HNO is the one electron reduced form of nitric oxide (NO), which has been indicated in a variety of processes in the body, including regulation of vascular tone and neuronal signaling. The rate of HNO release by Piloty′s acid at pH 7.0 is very slow (t½ = 5500 minutes), making its use most effective above pH 8.0. As pH increases, the half-life of Piloty′s acid decreases to 561, 90, and 33 minutes at pH 8.0, 9.0, and 10.0, respectively. Piloty′s acid also inhibits yeast aldehyde dehydrogenase (ALDH) with an IC50 of 48 muM.
Piloty′s Acid (CAS 599-71-3) References
- Mechanistic variations in the oxidation of Piloty's acid by metal complexes. | Wilkins, PC., et al. 2004. Inorg Chem. 43: 7877-81. PMID: 15554653
- The chemistry of nitroxyl-releasing compounds. | DuMond, JF. and King, SB. 2011. Antioxid Redox Signal. 14: 1637-48. PMID: 21235345
- Detection of nitroxyl (HNO) by membrane inlet mass spectrometry. | Cline, MR., et al. 2011. Free Radic Biol Med. 50: 1274-9. PMID: 21349325
- Mechanistic studies of the reactions of the reduced vitamin B12 derivatives with the HNO donor Piloty's acid: further evidence for oxidation of cob(I)alamin by (H)NO. | Subedi, H. and Brasch, NE. 2016. Dalton Trans. 45: 352-60. PMID: 26618754
- Development and cellular application of visible-light-controllable HNO releasers based on caged Piloty's acid. | Kawaguchi, M., et al. 2018. Chem Commun (Camb). 54: 10371-10374. PMID: 30152479
- Stoichiometric Nitroxyl Photorelease Using the (6-Hydroxy-2-naphthalenyl)methyl Phototrigger. | Zhou, Y., et al. 2019. Org Lett. 21: 1054-1057. PMID: 30694069
- A Mononuclear, Nonheme FeII-Piloty's Acid (PhSO2NHOH) Adduct: An Intermediate in the Production of {FeNO}7/8 Complexes from Piloty's Acid. | Confer, AM., et al. 2019. J Am Chem Soc. 141: 7046-7055. PMID: 30994347
- Piloty's acid and its hydrazide analogue: Insights from the density functional theory and vibrational spectroscopy on the conformational stability and chemical reactivity. | Al-Saadi, AA. 2021. Spectrochim Acta A Mol Biomol Spectrosc. 249: 119317. PMID: 33360061
- Mechanistic Studies on the Reaction between Aquacobalamin and the HNO Donor Piloty's Acid over a Wide pH Range in Aqueous Solution. | Polaczek, J., et al. 2021. Inorg Chem. 60: 2964-2975. PMID: 33513014
- Solid-gas reactions for nitroxyl (HNO) generation in the gas phase. | Carrone, G., et al. 2021. J Inorg Biochem. 223: 111535. PMID: 34298305
- Nitric oxide: a physiologic messenger molecule. | Bredt, DS. and Snyder, SH. 1994. Annu Rev Biochem. 63: 175-95. PMID: 7526779
- Prodrugs of nitroxyl as potential aldehyde dehydrogenase inhibitors vis-a-vis vascular smooth muscle relaxants. | Nagasawa, HT., et al. 1995. J Med Chem. 38: 1865-71. PMID: 7783118
- Oxidative release of nitric oxide accounts for guanylyl cyclase stimulating, vasodilator and anti-platelet activity of Piloty's acid: a comparison with Angeli's salt. | Zamora, R., et al. 1995. Biochem J. 312 (Pt 2): 333-9. PMID: 8526840
- Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and ugly. | Beckman, JS. and Koppenol, WH. 1996. Am J Physiol. 271: C1424-37. PMID: 8944624
- Synthesis, chemistry, and applications of nitroxyl ion releasers sodium trioxodinitrate or Angeli's salt and Piloty's acid. | Hughes, MN. and Cammack, R. 1999. Methods Enzymol. 301: 279-87. PMID: 9919577
Inhibitor of:
ALDH, and Enzyme.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Piloty′s Acid, 500 mg | sc-205436 | 500 mg | $20.00 | |||
Piloty′s Acid, 1 g | sc-205436A | 1 g | $32.00 |